Quality Assurance Analyst II

At Obie, we don’t just insure properties — we ensure progress. With advanced technology, real-time data, and a vast network of agents and partners, we help real estate investors and landlords get insurance coverage whenever and wherever they need it. Thousands of owners nationwide trust us to be the insurance experts, so they don’t have to be.

Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, and celebrate wins together. If you're passionate about driving change and eager to impact the real estate and insurance market, Obie is the place for you.

Our Chicago based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.

While Obie does offer fully remote opportunities for those outside of Chicagoland, we are only currently hiring in the following states: AZ, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NC, OH, PA, SC, SD, TN, TX, UT, WI

As a QA Analyst II, you will be responsible for collaborating with leaders and stakeholders across the company to understand the business, product and system requirements. Using both business and technical specs, you will create and execute test plans and test cases, and will be responsible for creating and maintaining QA artifacts. The QA Analyst II will provide support for multiple testing phases such as Smoke testing, End to End testing, User Acceptance testing, and Regression testing.

Those successful in this role will:

• Be strategic thinkers who are also detail‑oriented, organized, and collaborative
• Have the ability to negotiate skillfully with stakeholders to find common ground and acceptable alternatives that satisfy the needs of multiple end users
• Be adaptable in communication style to meet the needs of the intended audience (technical for engineers vs laymans terms for stakeholders vs executive summaries for leaders)
• Be familiar with agile methodologies and the SDLC/STLC for CI/CD

• Thoroughly test software to ensure proper operation and freedom from defects utilizing knowledge of application architecture
• Maintain documentation of test results, assist in debugging and communicate to business stakeholders
• Utilize necessary analytical skills to develop and maintain knowledge of in‑house/vendor systems, formulas, rate specifications, manual rules, and state filing information to identify unusual, inconsistent or error conditions
• Maintain a test repository and/or performance test results; identify and resolve problems in areas of test development/management; devise improvements to current procedures and develop models of possible future configurations
• Provide detailed, insightful, constructive, and actionable feedback based on testing outcomes; produce reporting and documentation for all testing efforts, results, activities, data, logging and tracking
• Create visibility and deepen collaboration during development to ensure more reliable releases
• Enhance tools, processes, and frameworks to bring insurance products to market

• Bachelor’s degree or equivalent required
• 3+ years experience developing, executing and monitoring application and business test cases;
• 3+ years experience in P&C insurance industry or insurtech preferred
• 1+ years experience creating test automation suites on web services preferred
• Expertise in reviewing/designing test cases, test strategies, and test plans for multiple application releases based upon decomposed technical and user requirements
• Experience and comfort within Salesforce, a Policy Administration System (PAS), GSuite and JIRA (or similar task management software);
• Familiarity with Java and Python, and tools such as Postman, Percy, and Playwrite
• Strong analytical techniques and technical communication skills with ability to communicate ideas clearly, concisely and effectively
• Ability to work in cross‑functional teams and communicate with colleagues in both business and technical roles
• Positive “can do” attitude and a desire to contribute to a growing, energetic working team; experience working within a fast paced agile software development environment
• Detail oriented with the ability to…